The Journal of Organic Chemistry
Article
Jin, Y.; Lee, K.; Kim, G.; Lee, K. Y.; Yang, J. S.; Shin, J. H.; Nam, K. Y.;
No, K. T.; Han, G. Eur. J. Med. Chem. 2008, 43, 1519.
ACKNOWLEDGMENTS
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We thank the National Science Foundation (CHE-1240194/
CenSURF) for lignin-related work and NSF (CBET 1262176)
for the development of indirect electrochemical methods.
(12) (a) Blair, A.; Stevenson, L.; Sutherland, A. Tetrahedron Lett. 2012,
5
3, 4084. (b) Takos, A. M.; Rook, F. Int. J. Mol. Sci. 2013, 14, 11713.
(c) Nakagawa, A.; Minami, H.; Kim, J. − S.; Koyanagi, T.; Katayama, T.;
Sato, F.; Kumagai, H. Nat. Commun. 2011, 2, 326.
(
13) Please see: Tsvelikhovsky, D.; Buchwald, S. L. J. Am. Chem. Soc.
REFERENCES
■
2
011, 133, 14228 and references therein..
(
1) Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B.
M. Chem. Rev. 2010, 110, 3552.
(14) For examples of related polymers, see: Hu, L.; Graaf, M. D.;
Moeller, K. D. J. Electrochem. Soc. 2013, 160, G3020.
(15) Please see: Yang, Y.; Philips, D.; Pan, S. J. Org. Chem. 2011, 76,
(
(
2) Calvo-Flores, F. G.; Dobado, J. A. ChemSusChem 2010, 3, 1227.
3) Tuck, C. O.; Perez, E.; Horvath, I. T.; Sheldon, R. A.; Poliakoff, M.
́
́
1902 and references therein..
Science 2012, 337, 695.
4) Azadi, P.; Inderwildi, O. R.; Farnood, R.; King, D. A. Renewable
Sustainable Energy Rev. 2013, 21, 506.
5) Ragauskas, A. J.; Beckham, G. T.; Biddy, M. J.; Chandra, R.; Chen,
F.; Davis, M. F.; Davison, B. H.; Dixon, R. A.; Gilna, P.; Keller, M.;
Langan, P.; Nskar, A. K.; Saddler, J. N.; Tschaplinski, T. J.; Tuskan, G.
A.; Wyman, C. E. Science 2014, 344, 709.
(16) For reviews, see: (a) Frontana-Uribe, B. A.; Little, R. D.; Ibanez, J.
G.; Palma, A.; Vasquez-Medrano, R. Green Chem. 2010, 12, 2099.
(b) Yoshida, J.; Kataoka, K.; Horcajada, R.; Nagaki, A. Chem. Rev. 2008,
108, 2265. (c) Sperry, J. B.; Wright, D. L. Chem. Soc. Rev. 2006, 35, 605.
(17) (a) Vanden Eynde, J. J.; Delfosse, F.; Lor, P.; Van Haverbeke, Y.
Tetrahedron 1995, 51, 5813−5818. (b) Bahrami, K.; Khodaei, M. M.;
Naali, F. J. Org. Chem. 2008, 73, 6835.
(
(
(
6) For a review of early work, see ref 1. For selected recent examples
(18) For the initial development of the indirect method, see: Nguyen,
B. H.; Kesselring, D.; Tesfu, E.; Moeller, K. D. Langmuir 2014, 30, 2280.
(19) For direct oxidations using sunlight as the source of electricity,
see: Anderson, L. A.; Redden, A.; Moeller, K. D. Green Chem. 2011, 13,
1652.
(20) For indirect oxidations using sunlight as the source of electricity,
see: Nguyen, B. H.; Redden, A.; Moeller, K. D. Green Chem. 2014, 16,
69.
(21) For reviews of indirect electrochemical methods, see: (a) Ogibin,
Y. N.; Elinson, M. N.; Nikishin, G. I. Russ. Chem. Rev. 2009, 78, 89.
(b) Simonet, J.; Pilard, J. -F. In Organic Electrochemistry, 4th ed., Revised
and Expanded; Lund, H., Hammerich, O., Eds.; Marcel Dekker: New
York, 2001; p 1163.
see: (a) Bharathiraja, B.; Sudharsanaa, T.; Bharghavi, A.; Sowmeya, G. S.;
Balaram, G. Int. J. ChemTech Res. 2014, 6 (9), 4334. (b) Feghali, E.;
Cantat, T. Chem. Commun. 2014, 50, 862. (c) Barta, K.; Warner, G. R.;
Beach, E. S.; Anastas, P. T. Green Chem. 2014, 16, 191. (e) Song, Q.;
Wang, F.; Cai, J.; Wang, Y.; Zhang, J.; Yu, W.; Xu, J. Energy Environ. Sci.
2
013, 6, 994. (f) Sturgeon, M. R.; O’Brien, M. H.; Ciesielski, P. N.;
Katahira, R.; Kruger, J. S.; Chmely, S. C.; Hamlin, J.; Lawrence, K.;
Hunsinger, G. B.; Foust, T. D.; Baldwin, R. M.; Biddy, M. J.; Beckham,
G. T. Green Chem. 2014, 16, 824. (g) Zhang, J.; Chen, Y.; Brook, M. A.
ACS Sustainable Chem. Eng. 2014, 2, 1983 and references therein..
(
7) For a review of early work see ref 1. For selected recent examples
see: (a) Lim, S. H.; Nahm, K.; Ra, C. S.; Cho, D. W.; Yoon, U. C.;
Latham, J. A.; Dunaway-Mariano, D.; Mariano, P. S. J. Org. Chem. 2013,
(22) Smith, J. A.; Moeller, K. D. Org. Lett. 2013, 15, 5818.
(
23) (a) For a review of early work, see: Moeller, K. D. Synlett 2009,
009, 1208. (b) For more recent efforts, see: Redden, A.; Perkins, R. J.;
Moeller, K. D. Angew. Chem., Int. Ed. 2013, 52, 12865.
24) Jiang, X.; Wang, J.-M.; Zhang, Y.; Chen, Z.; Zhu, Y.-M.; Ji, S.-J.
Org. Lett. 2014, 16 (13), 3492.
25) Terazzi, E.; Torelli, S.; Bernardinelli, G.; Rivera, J.-P.; Benech, J.-
7
8, 9431. (b) Cho, D. W.; Latham, J. A.; Park, H. J.; Yoon, U. C.; Langan,
P.; Dunaway-Mariano, D.; Mariano, P. S. J. Org. Chem. 2011, 76, 2840.
c) Nguyen, J. D.; Matsuura, B. S.; Stephenson, C. R. J. J. Am. Chem. Soc.
2
(
(
2014, 136, 1218. (d) Kansal, S. K.; Singh, M.; Sud, D. J. Hazard. Mater.
2008, 153 (1−2), 412. (e) Prado, R.; Erdocia, X.; Labidi, J. Chemosphere
2013, 91 (9), 1355. (f) Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl,
(
M.; Bourgogne, C.; Donnio, B.; Guillon, D.; Imbert, D.; Buenzli, J-.C.G.;
Pinto, A.; Jeannerat, D.; Piguet, C. J. Am. Chem. Soc. 2005, 127 (3), 888.
S. S. J. Am. Chem. Soc. 2013, 135, 6415.
8) (a) Wang, H.; Tucker, M.; Ji, Y. J. Appl. Chem. 2013, 2013, 1−9.
b) Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl, S. S. Nature 2014, 515, 249.
(
(
26) Janaswamy, R. M.; Geereddy, B. R.; Vidadala, R. S. R.; Puppala, M.
PCT Int. Appl. 2011117706, Sep 29, 2011.
27) Hattori, M.; Yang, X. W.; Shu, Y. Z.; Kakiuchi, N.; Tezuka, Y.;
Kikuchi, T.; Namba, T. Chem. Pharm. Bull. 1988, 36 (2), 648.
28) Ito, C.; Itoigawa, M.; Otsuka, T.; Tokuda, H.; Nishino, H.;
(
(
(
9) Gellerstedt, G.; Northey, R. A. Wood Sci. Technol. 1989, 23, 75.
10) For benzimidazoles, see: (a) Cole, D. C.; Gross, J. L.; Cornery, T.
(
A.; Aschmies, S.; Hirst, W. D.; Kelley, C.; Kin, J. I.; Kubek, K.; Ning, X.;
Platt, B. J.; Robichaud, A. J.; Solvibile, W. R.; Stock, J. R.; Tawa, G.;
Williams, M. J.; Ellingboe, J. W. Bioorg. Med. Chem. Lett. 2010, 20, 1237.
(
Furukawa, H. J. Nat. Prod. 2000, 63, 1344−1348.
(
(
29) Faler, C. A.; Joullie, M. M. Org. Lett. 2007, 9 (10), 1987.
30) Davis, R.; Saleesh Kumar, N. S.; Abraham, S.; Suresh, C. H.; Rath,
(
b) Bressi, J. C.; de Jong, R.; Wu, Y.; Jennings, A. J.; Brown, J. W.;
O’Connell, S.; Tari, L. W.; Skene, R. J.; Vu, P.; Navre, M.; Cao, X.;
Gangloff, A. R. Bioorg. Med. Chem. Lett. 2010, 20, 3138. (c) Penning, T.
D.; Zhu, G. D.; Gandhi, V. B.; Gong, J.; Liu, X.; Shi, Y.; Klinghofer, B.;
Johnson, E. F.; Donawho, C. K.; Frost, D. J.; Bontcheva-Diaz, V.;
Bouska, J. J.; Osterling, D. J.; Olson, A. M.; Marsh, K. C.; Luo, Y.;
Giranda, V. L. J. Med. Chem. 2009, 52 (2), 514. (d) Yenjerla, M.; Cox, C.;
Wilson, L.; Jordan, M. A. J. J. Pharmacol. Exp. Ther. 2009, 328, 390.
N. P.; Tamaoki, N.; Das, S. J. Phys. Chem. C 2008, 112 (6), 2137.
31) Sinha, A. K.; Joshi, B. P.; Sharma, A. U.S. Patent 20040118673,
Jun 24, 2004.
32) Kang, B.-R; Wang, J.; Li, H.; Li, Y.; Mei, Q.-B.; Zhang, S.-Q. Med.
Chem. Res. 2014, 23 (3), 1340.
(
(
(
11) For benzthiazoles, see: (a) Carpenter, R. D.; Andrei, M.; Aina, O.
H.; Lau, E. Y.; Lightstone, F. C.; Liu, R.; Lam, K. S.; Kurth, M. J. J. Med.
Chem. 2009, 52 (1), 14. (b) Ammazzalorso, A.; Giancristofaro, A.;
Angelo, A.; De Filippis, B.; Fantacuzzi, M.; Giampietro, L.; Maccallini,
C.; Amoroso, R. Bioorg. Med. Chem. Lett. 2011, 21, 4869. (c) Vu, C. B.;
Milne, J. C.; Carney, D. P.; Song, J.; Choy, W.; Lambert, P. D.; Gagne, D.
J.; Hirsch, M.; Cote, A.; Davis, M.; Lainez, E.; Meade, M.; Normington,
K.; Jirousek, M. R.; Perni, R. B. Bioorg. Med. Chem. Lett. 2009, 19, 1416.
(
d) Bowyer, P. W.; Gunaratne, R. S.; Grainger, M.; Withers-Martinez,
C.; Wickramsinghe, S. R.; Tate, E. W.; Leatherbarrow, R. J.; Brown, K.
A.; Holder, A. A.; Smith, D. F. Biochem. J. 2007, 408, 173. (e) Stevens, M.
F. G.; McCall, C. J.; Lelievald, P.; Alexander, P.; Richter, A.; Davies, D. E.
J. Med. Chem. 1994, 37 (11), 1689. (f) Bradshaw, T. D.; Westwell, A. D.
Curr. Med. Chem. 2004, 11, 1009. (g) Song, E. Y.; Kaur, N.; Park, K. M.;
J
J. Org. Chem. XXXX, XXX, XXX−XXX